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Peter Winterhalter - One of the best experts on this subject based on the ideXlab platform.
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anthocyanin composition of black carrot daucus carota ssp sativus var atrorubens alef cultivars antonina beta sweet deep purple and purple haze
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Elyana Cuevas Montilla, Miriam Rodriguez Arzaba, Silke Hillebrand, Peter WinterhalterAbstract:This study aimed to identify the pigment composition of black carrot (Daucus carota ssp. sativus var. atrorubens Alef.) cultivars Antonina, Beta Sweet, Deep Purple, and Purple Haze. Cyanidin 3-xylosyl(glucosyl)Galactosides acylated with sinapic acid, ferulic acid, and coumaric acid were detected as major anthocyanins by high-performance liquid chromatography with diode array detection (HPLC-DAD) and with electrospray ionization multiple mass spectrometry (HPLC-ESI-MSn) analyses. The preparative isolation of these pigments was carried out by means of high-speed countercurrent chromatography (HSCCC). The color activity concept was applied to the isolated anthocyanins at three pH values. Cyanidin 3-xylosyl(sinapoylglucosyl)Galactoside was found to exhibit a lower visual detection threshold and a higher pH stability than cyanidin 3-xylosyl(feruloylglucosyl)Galactoside and cyanidin 3-xylosyl(coumaroylglucosyl)Galactoside. The color parameters of the fresh roots of the four cultivars were described by the CIELa...
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anthocyanin composition of black carrot daucus carota ssp sativus var atrorubens alef cultivars antonina beta sweet deep purple and purple haze
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Elyana Cuevas Montilla, Miriam Rodriguez Arzaba, Silke Hillebrand, Peter WinterhalterAbstract:This study aimed to identify the pigment composition of black carrot (Daucus carota ssp. sativus var. atrorubens Alef.) cultivars Antonina, Beta Sweet, Deep Purple, and Purple Haze. Cyanidin 3-xylosyl(glucosyl)Galactosides acylated with sinapic acid, ferulic acid, and coumaric acid were detected as major anthocyanins by high-performance liquid chromatography with diode array detection (HPLC-DAD) and with electrospray ionization multiple mass spectrometry (HPLC-ESI-MS(n)) analyses. The preparative isolation of these pigments was carried out by means of high-speed countercurrent chromatography (HSCCC). The color activity concept was applied to the isolated anthocyanins at three pH values. Cyanidin 3-xylosyl(sinapoylglucosyl)Galactoside was found to exhibit a lower visual detection threshold and a higher pH stability than cyanidin 3-xylosyl(feruloylglucosyl)Galactoside and cyanidin 3-xylosyl(coumaroylglucosyl)Galactoside. The color parameters of the fresh roots of the four cultivars were described by the CIELab coordinates L* (lightness), C* (chroma), and h(ab) (hue angles). Total phenolics varied among the cultivars and ranged from 17.9 to 97.9 mg gallic acid equivalents (GAE)/100 g fresh weight (fw). For the content of monomeric anthocyanins, values between 1.5 and 17.7 mg/100 g fw were determined.
Elyana Cuevas Montilla - One of the best experts on this subject based on the ideXlab platform.
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anthocyanin composition of black carrot daucus carota ssp sativus var atrorubens alef cultivars antonina beta sweet deep purple and purple haze
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Elyana Cuevas Montilla, Miriam Rodriguez Arzaba, Silke Hillebrand, Peter WinterhalterAbstract:This study aimed to identify the pigment composition of black carrot (Daucus carota ssp. sativus var. atrorubens Alef.) cultivars Antonina, Beta Sweet, Deep Purple, and Purple Haze. Cyanidin 3-xylosyl(glucosyl)Galactosides acylated with sinapic acid, ferulic acid, and coumaric acid were detected as major anthocyanins by high-performance liquid chromatography with diode array detection (HPLC-DAD) and with electrospray ionization multiple mass spectrometry (HPLC-ESI-MSn) analyses. The preparative isolation of these pigments was carried out by means of high-speed countercurrent chromatography (HSCCC). The color activity concept was applied to the isolated anthocyanins at three pH values. Cyanidin 3-xylosyl(sinapoylglucosyl)Galactoside was found to exhibit a lower visual detection threshold and a higher pH stability than cyanidin 3-xylosyl(feruloylglucosyl)Galactoside and cyanidin 3-xylosyl(coumaroylglucosyl)Galactoside. The color parameters of the fresh roots of the four cultivars were described by the CIELa...
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anthocyanin composition of black carrot daucus carota ssp sativus var atrorubens alef cultivars antonina beta sweet deep purple and purple haze
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Elyana Cuevas Montilla, Miriam Rodriguez Arzaba, Silke Hillebrand, Peter WinterhalterAbstract:This study aimed to identify the pigment composition of black carrot (Daucus carota ssp. sativus var. atrorubens Alef.) cultivars Antonina, Beta Sweet, Deep Purple, and Purple Haze. Cyanidin 3-xylosyl(glucosyl)Galactosides acylated with sinapic acid, ferulic acid, and coumaric acid were detected as major anthocyanins by high-performance liquid chromatography with diode array detection (HPLC-DAD) and with electrospray ionization multiple mass spectrometry (HPLC-ESI-MS(n)) analyses. The preparative isolation of these pigments was carried out by means of high-speed countercurrent chromatography (HSCCC). The color activity concept was applied to the isolated anthocyanins at three pH values. Cyanidin 3-xylosyl(sinapoylglucosyl)Galactoside was found to exhibit a lower visual detection threshold and a higher pH stability than cyanidin 3-xylosyl(feruloylglucosyl)Galactoside and cyanidin 3-xylosyl(coumaroylglucosyl)Galactoside. The color parameters of the fresh roots of the four cultivars were described by the CIELab coordinates L* (lightness), C* (chroma), and h(ab) (hue angles). Total phenolics varied among the cultivars and ranged from 17.9 to 97.9 mg gallic acid equivalents (GAE)/100 g fresh weight (fw). For the content of monomeric anthocyanins, values between 1.5 and 17.7 mg/100 g fw were determined.
Silke Hillebrand - One of the best experts on this subject based on the ideXlab platform.
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anthocyanin composition of black carrot daucus carota ssp sativus var atrorubens alef cultivars antonina beta sweet deep purple and purple haze
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Elyana Cuevas Montilla, Miriam Rodriguez Arzaba, Silke Hillebrand, Peter WinterhalterAbstract:This study aimed to identify the pigment composition of black carrot (Daucus carota ssp. sativus var. atrorubens Alef.) cultivars Antonina, Beta Sweet, Deep Purple, and Purple Haze. Cyanidin 3-xylosyl(glucosyl)Galactosides acylated with sinapic acid, ferulic acid, and coumaric acid were detected as major anthocyanins by high-performance liquid chromatography with diode array detection (HPLC-DAD) and with electrospray ionization multiple mass spectrometry (HPLC-ESI-MSn) analyses. The preparative isolation of these pigments was carried out by means of high-speed countercurrent chromatography (HSCCC). The color activity concept was applied to the isolated anthocyanins at three pH values. Cyanidin 3-xylosyl(sinapoylglucosyl)Galactoside was found to exhibit a lower visual detection threshold and a higher pH stability than cyanidin 3-xylosyl(feruloylglucosyl)Galactoside and cyanidin 3-xylosyl(coumaroylglucosyl)Galactoside. The color parameters of the fresh roots of the four cultivars were described by the CIELa...
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anthocyanin composition of black carrot daucus carota ssp sativus var atrorubens alef cultivars antonina beta sweet deep purple and purple haze
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Elyana Cuevas Montilla, Miriam Rodriguez Arzaba, Silke Hillebrand, Peter WinterhalterAbstract:This study aimed to identify the pigment composition of black carrot (Daucus carota ssp. sativus var. atrorubens Alef.) cultivars Antonina, Beta Sweet, Deep Purple, and Purple Haze. Cyanidin 3-xylosyl(glucosyl)Galactosides acylated with sinapic acid, ferulic acid, and coumaric acid were detected as major anthocyanins by high-performance liquid chromatography with diode array detection (HPLC-DAD) and with electrospray ionization multiple mass spectrometry (HPLC-ESI-MS(n)) analyses. The preparative isolation of these pigments was carried out by means of high-speed countercurrent chromatography (HSCCC). The color activity concept was applied to the isolated anthocyanins at three pH values. Cyanidin 3-xylosyl(sinapoylglucosyl)Galactoside was found to exhibit a lower visual detection threshold and a higher pH stability than cyanidin 3-xylosyl(feruloylglucosyl)Galactoside and cyanidin 3-xylosyl(coumaroylglucosyl)Galactoside. The color parameters of the fresh roots of the four cultivars were described by the CIELab coordinates L* (lightness), C* (chroma), and h(ab) (hue angles). Total phenolics varied among the cultivars and ranged from 17.9 to 97.9 mg gallic acid equivalents (GAE)/100 g fresh weight (fw). For the content of monomeric anthocyanins, values between 1.5 and 17.7 mg/100 g fw were determined.
Miriam Rodriguez Arzaba - One of the best experts on this subject based on the ideXlab platform.
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anthocyanin composition of black carrot daucus carota ssp sativus var atrorubens alef cultivars antonina beta sweet deep purple and purple haze
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Elyana Cuevas Montilla, Miriam Rodriguez Arzaba, Silke Hillebrand, Peter WinterhalterAbstract:This study aimed to identify the pigment composition of black carrot (Daucus carota ssp. sativus var. atrorubens Alef.) cultivars Antonina, Beta Sweet, Deep Purple, and Purple Haze. Cyanidin 3-xylosyl(glucosyl)Galactosides acylated with sinapic acid, ferulic acid, and coumaric acid were detected as major anthocyanins by high-performance liquid chromatography with diode array detection (HPLC-DAD) and with electrospray ionization multiple mass spectrometry (HPLC-ESI-MSn) analyses. The preparative isolation of these pigments was carried out by means of high-speed countercurrent chromatography (HSCCC). The color activity concept was applied to the isolated anthocyanins at three pH values. Cyanidin 3-xylosyl(sinapoylglucosyl)Galactoside was found to exhibit a lower visual detection threshold and a higher pH stability than cyanidin 3-xylosyl(feruloylglucosyl)Galactoside and cyanidin 3-xylosyl(coumaroylglucosyl)Galactoside. The color parameters of the fresh roots of the four cultivars were described by the CIELa...
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anthocyanin composition of black carrot daucus carota ssp sativus var atrorubens alef cultivars antonina beta sweet deep purple and purple haze
Journal of Agricultural and Food Chemistry, 2011Co-Authors: Elyana Cuevas Montilla, Miriam Rodriguez Arzaba, Silke Hillebrand, Peter WinterhalterAbstract:This study aimed to identify the pigment composition of black carrot (Daucus carota ssp. sativus var. atrorubens Alef.) cultivars Antonina, Beta Sweet, Deep Purple, and Purple Haze. Cyanidin 3-xylosyl(glucosyl)Galactosides acylated with sinapic acid, ferulic acid, and coumaric acid were detected as major anthocyanins by high-performance liquid chromatography with diode array detection (HPLC-DAD) and with electrospray ionization multiple mass spectrometry (HPLC-ESI-MS(n)) analyses. The preparative isolation of these pigments was carried out by means of high-speed countercurrent chromatography (HSCCC). The color activity concept was applied to the isolated anthocyanins at three pH values. Cyanidin 3-xylosyl(sinapoylglucosyl)Galactoside was found to exhibit a lower visual detection threshold and a higher pH stability than cyanidin 3-xylosyl(feruloylglucosyl)Galactoside and cyanidin 3-xylosyl(coumaroylglucosyl)Galactoside. The color parameters of the fresh roots of the four cultivars were described by the CIELab coordinates L* (lightness), C* (chroma), and h(ab) (hue angles). Total phenolics varied among the cultivars and ranged from 17.9 to 97.9 mg gallic acid equivalents (GAE)/100 g fresh weight (fw). For the content of monomeric anthocyanins, values between 1.5 and 17.7 mg/100 g fw were determined.
Ulf J Nilsson - One of the best experts on this subject based on the ideXlab platform.
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C1-Galactopyranosyl Heterocycle Structure Guides Selectivity: Triazoles Prefer Galectin‑1 and Oxazoles Prefer Galectin‑3
2019Co-Authors: Alexander Dahlqvist, Hakon Leffler, Ulf J NilssonAbstract:Galectins are carbohydrate-recognizing proteins involved in many different pathological processes, including cancer and immune-related disorders. Inhibitors of galectins have evolved from natural oligosaccharides toward more drug-like truncated Galactoside scaffolds that only retain key specific interactions of the galactose scaffolds with the galectin carbohydrate recognition domains. In this context, C1-Galactosides are attractive and stable scaffolds, and this work reports that the synthesis of novel C1-galactopyranosyl heteroaryl derivatives as galectin inhibitors, in which galectin selectivity is governed by the composition of the heterocycle and affinity, is driven by the structure of the aryl substituent to give compounds selective for either galectin-1 or galectin-3. The affinities are close to or better than those of lactose and other natural galectin-binding disaccharides, selectivities induced by the C1-heteroaryl groups are superior to lactose, and compound hydrolytic stabilities and drug-like properties are potentially better than those of natural saccharides. Hence, C1-galactopyranosyl heteroaryls constitute a class of promising starting scaffolds for galectin inhibition, in which a natural ligand pyranose has been replaced by more than fivefold selectivity-inducing heteroaryl rings leading to affinities of 90 μM toward galectin-3 for a C1-galactopyranosyl naphthyloxazole and 170 μM toward galectin-1 for a C1-galactopyranosyl 2-fluorophenyltriazole
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cobalt mediated solid phase synthesis of 3 o alkynylbenzyl Galactosides and their evaluation as galectin inhibitors
Tetrahedron, 2006Co-Authors: Anders Bergh, Hakon Leffler, Ulf J Nilsson, Anders Sundin, Nina KannAbstract:Methyl beta-D-Galactoside was converted to the corresponding 3,4-O-stannylene acetal, which was selectively benzylated with 3-iodobenzyl bromide and coupled to a polymer-bound propargylic ether via a Sonogashira reaction. The polymer-bound carbohydrate substrate was cleaved from the resin with different carbon nucleophiles in a cobalt-mediated Nicholas reaction. The product 3-O-alkynylbenzyl Galactosides were screened towards galectin-1, -3, -7, -8N and -9N in a competitive fluorescence polarisation assay. Particularly potent inhibitors were identified against galectin-7 with affinity enhancements up to one order of magnitude due to the 3-O-alkynylbenzyl moiety. (c) 2006 Elsevier Ltd. All rights reserved.
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3 1 2 3 triazol 1 yl 1 thio Galactosides as small efficient and hydrolytically stable inhibitors of galectin 3
ChemInform, 2005Co-Authors: Bader A Salameh, Hakon Leffler, Ulf J NilssonAbstract:Copper(I)-catalyzed addition of alkynes to methyl 3-azido-3-deoxy-1-thio-beta-D-galactopyranoside afforded stable and structurally simple 3-deoxy-3-(1H-1,2,3-triazol-1-yl)-1-thio-Galactosides carrying a panel of substituents at the triazole C4 in high yields. The 3-(1H-[1,2,3]-triazol-1-yl)-1-thio-Galactoside collection synthesized contained inhibitors of the tumor- and inflammation-related galectin-3 with Kd values as low as 107 microM, which is as potent as the natural disaccharide inhibitors lactose and N-acetyllactosamine.
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3 1 2 3 triazol 1 yl 1 thio Galactosides as small efficient and hydrolytically stable inhibitors of galectin 3
Bioorganic & Medicinal Chemistry Letters, 2005Co-Authors: Bader A Salameh, Hakon Leffler, Ulf J NilssonAbstract:Copper(I)-catalyzed addition of alkynes to methyl 3-azido-3-deoxy-1-thio-β-d-galactopyranoside afforded stable and structurally simple 3-deoxy-3-(1H-1,2,3-triazol-1-yl)-1-thio-Galactosides carrying a panel of substituents at the triazole C4 in high yields. The 3-(1H-[1,2,3]-triazol-1-yl)-1-thio-Galactoside collection synthesized contained inhibitors of the tumor- and inflammation-related galectin-3 with Kd values as low as 107 μM, which is as potent as the natural disaccharide inhibitors lactose and N-acetyllactosamine.
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synthesis of a phenyl thio d galactopyranoside library from 1 5 difluoro 2 4 dinitrobenzene discovery of efficient and selective monosaccharide inhibitors of galectin 7
Organic and Biomolecular Chemistry, 2005Co-Authors: Ian Cumpstey, Hakon Leffler, Susanne Carlsson, Ulf J NilssonAbstract:The galectins are a family of β-Galactoside-binding proteins that have been implicated in cancer and inflammation processes. Herein, we report the synthesis of a library of 28 compounds that was tested for binding to galectins-1, -3, -7, -8N and -9N. An aromatic nucleophilic substitution reaction between 1,5-difluoro-2,4-dinitrobenzene and a galacto thiol gave 5-fluoro-2,4-dinitrophenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside. This versatile intermediate was then modified in a two dimensional manner: either by further substitution of the second fluoride by amines or thiols, or by reduction of the nitro groups and acylation of the resulting amines, or both. Deacetylation then gave a library of aromatic β-Galactosides that showed variable inhibitory activity against the different galectins, as shown by screening with a fluorescence-polarisation assay. Particularly efficient inhibitors were found against galectin-7, while less impressive enhancements of inhibitor affinity over methyl β-D-galactopyranoside were found for galectin-1, -3, -8N and -9N. The best inhibitors against galectin-7 showed significantly higher affinity (Kd as low as 140 µM) than both β-methyl Galactoside (Kd 4.8 mM) and the unsubstituted β-phenyl thioGalactoside (non-inhibitory). The best inhibitors against galectin-7 were poor against the other galectins and thus have potential as structurally simple and selective tools for dissecting biological functions of galectin-7.
